Hydrochloric Acid → 2-((2-Benzoylphenylthio)methyl)-2-ethylhexanal

HRID 478882

Reaktionsgleichung

Reaktionsgleichung von HRID 478882
[SH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:16]([C:18]([CH2:25]OS(C)(=O)=O)([CH2:21][CH2:22][CH2:23][CH3:24])[CH:19]=[O:20])[CH3:17].C(N(CC)CC)C.Cl>COCCOCCOC>[C:4]([C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[S:1][CH2:25][C:18]([CH2:16][CH3:17])([CH2:21][CH2:22][CH2:23][CH3:24])[CH:19]=[O:20])(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 34997132-MercaptobenzophenoneHCID 115722172-Ethyl-2-(mesyloxymethyl)hexanal

Produkt 1

HCID 116028262-((2-Benzoylphenylthio)methyl)-2-ethylhexanalAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Versuchsvorschrift

A mixture of 31 g (0.144 mol) of 2-mercaptobenzophenone, prepared according to the procedure described in WO 93/16055, 24.4 g (0.1 mole) of 2-ethyl-2-(mesyloxymethyl)-hexanal (1), 14.8 g (0.146 mole) of triethylamine, and 80 mL of 2-methoxyethyl ether was held at reflux for 24 h. The reaction mixture was poured into 3N HCl and extracted with 300 mL of methylene chloride, The methylene chloride layer was washed with 300 mL of 10% NaOH, dried over MgSO4 and concentrated in vacuo to remove 2-methoxyethyl ether. The residue was purified by HPLC (10% EtOAc-hexane) to give 20.5 g (58%) of 2 as an oil.

Aufarbeitung

  1. customprepared
  2. temperatureat reflux for 24 h
  3. extractionextracted with 300 mL of methylene chloride
  4. washThe methylene chloride layer was washed with 300 mL of 10% NaOH
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto remove 2-methoxyethyl ether
  8. customThe residue was purified by HPLC (10% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3ba2a7f111dd4316b2eab3ac37c46b53
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642268B2

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